Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/20—Carboxylic acid amides
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S260/00—Chemistry of carbon compounds
  • Y10S260/15—Antistatic agents not otherwise provided for
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S260/00—Chemistry of carbon compounds
  • Y10S260/15—Antistatic agents not otherwise provided for
  • Y10S260/19—Non-high polymeric antistatic agents/n
• • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
  • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
  • Y10S524/00—Synthetic resins or natural rubbers -- part of the class 520 series
  • Y10S524/91—Antistatic compositions

Definitions

• This invention relates to antistatic compositions of high molecular weight linear aliphatic polyamides which are stabilized against yellowing due to the action of heat.
• These polyamides which may be formed into films or fibers, are prepared by the solvent-free condensation of salts of aliphatic diamines with aliphatic dicarboxylic acids and/or lactams and contain homogeneously distributed therein a composition of one or more polyoxyalkylene compounds and tertiary amides or diamides, having at least one tertiary amide group.
• the amides or diamides may be prepared by the reaction of monocarboxylic acids or their derivatives with secondary amines or primary-secondary or disecondary diamines.
• antistatic polyamides which contain polyethers is their tendency to become yellow under the action of heat.
• polyether-containing aliphatic polyamides may be stabilized against yellowing by the addition of carboxylic acid amides, which are known antistatic agents, preferably the amides of secondary amines. In some cases the addition of less than 1%, by weight, is sufficient to import this stabilization. It is well known that this level of addition alone is not sufficient to render polyamides permanently antistatic.
• carboxylic acid amides which are known antistatic agents, preferably the amides of secondary amines.
• This invention therefore relates to aliphatic polyamides with reduced surface resistance which are stabilized against the yellowing produced by the action of heat, which polyamides have been obtained by the condensation of salts of aliphatic diamines with aliphatic dicarboxylic acids and/or lactams in solvent-free melt and which polyamides contain up to 7 %, by weight, of one or more polyoxyalkylene compounds and from 0.1 to 7 %, by weight, of a carboxylic acid amide of one of the following general formulae: ##EQU1## Wherein R and R 5 denote the same or different C 4 - C 24 alkyl group,
• R 1 denotes a C 1 - C 5 alkyl group
• R 2 denotes a C 6 - C 24 alkyl group
• R 3 denotes a C 1 - C 6 alkylene group
• R 4 denotes hydrogen or a C 1 - C 5 alkyl group.
• the invention also relates to a process for producing aliphatic polyamide compositions with reduced electrical surface resistance which are stabilized against yellowing due to heat, wherein tertiary amides or diamides which contain at least one tertiary amide group and correspond to one of the following general formulae ##EQU2## wherein R, R 1 , R 2 , R 3 , R 4 , and R 5 , are as defined above, are added in quantities of from 0.1 to 7 %, by weight, and one or more polyoxyalkylene compounds are added in quantities of up to 7%, by weight, to the polyamides obtained by condensation of salts of aliphatic diamines with aliphatic dicarboxylic acids and/or lactams in the melt, and are homogeneously distributed therein.
• the antistatic polyamide compositions of the present invention are stabilized against yellowing by heat, in spite of the fact that they contain polyoxyalkylene compounds. 2.
• the polyether content may be reduced without thereby adversely affecting the antistatic characteristics, with the result that disturbances in the spinning and stretching process are eliminated in the production of fibers from these polyamide compositions.
• the proportion of polyether-free antistatic agent may also be reduced since the antistatic effect of the amide component is increased by the synergistic effect between the polyether and the carboxylic acid amides.
• the aliphatic polyamide compositions of the present invention which are antistatic and stabilized against yellowing, may be used for producing shaped products, in particular fibers and sheets.
• the antistatically active polyoxyalkylene compounds may be incorporated into the polyamides, for example, by stirring them into the melt.
• the polyoxyalkylene compounds are first mixed with the polyamide melt and the mixture is then worked-up to a granulate to which other additives may be added before it is finally used.
• the polyethers may be added to the monomers before polymerisation is completed, provided that their chemical composition allows this without decomposition.
• Another method consists of first preparing a concentrate of the polyether in the polyamide with a polyoxyalkylene content of up to 30 %, by weight, and subsequently adding this concentrate to the polyamide melt in the desired concentration.
• the tertiary carboxylic acid amides used according to the invention which stabilize against yellowing and have an enhanced antistatic action due to the synergistic effect, may, in principle, be added to the polyamide in the manner described above. However, it must be taken into account that if the carboxylic acid amides are left too long in the melt they become ineffective due to amide interchange. This is almost invariably the case if a granulate containing both components is first prepared and then the final product is produced from it, because in that case the material must be melted twice.
• a granulate which contains polyether is first prepared and when this is being worked-up into fibers or sheets in an extruder, it is homogeneously mixed with a melt of carboxylic acid amides which is injected into the extruder just before the spinning or sheet -- forming stage.
• polyethers and carboxylic acid amides may, of course, also be carried out simultaneously by injection into the polyamide melt.
• Aliphatic polyamides which are suitable for use as starting materials for producing the present antistatic polyamide compositions which are stabilized against yellowing are linear polyamides or copolyamides which have recurrent structural units corresponding to one of the following general formulae: ##EQU3## Wherein R 6 denotes a straight or branched chain C 4 - C 20 alkylene group,
• R 7 denotes a straight or branched chain alkylene group, a cyclohexylene group or ##SPC1##
• R 8 denotes a straight or branched chain C 3 - C 20 alkylene group.
• Polycaprolactam and polyamide-66 are particularly preferred starting materials for producing the polyamide compositions of the present invention.
• Suitable carboxylic acid amides contain at least one tertiary amide group. They may be obtained from C 4 -C 25 monocarboxylic acids and secondary amines, with a short chain and a long chain N-alkyl group, or primary secondary diamines or disecondary diamines with one or two short chain N-alkyl groups.
• the preferred monocarboxylic acids are lauric acid, myristic acid and stearic acid and derivatives thereof which are capable of reacting with amines.
• N-methyl-dodecylamine and N-methyl-stearylamine are suitable secondary amines.
• diamines which may be used: N-methyl-ethylene diamine, N-methyl-diaminopropane, N-isopropyl-diaminohexane, N-isobutyl-diaminohexane, N,N'-dimethyl-ethylene diamine, N,N'-diethyl-diaminohexane, N,N'-diisopropyl-diaminohexane, N,N'-diisobutyl-diaminohexane, N,N'-dibenzyl-diaminohexane and N,N',N"-trimethyl-diethylene triamine.
• Diamides of primary-secondary diamines are particularly suitable because they have a very marked synergistic effect.
• the carboxylic acid amides should be present in the polyamide in quantities of from 0.1 to 7 %, by weight, quantities of from 1 to 3 %, by weight, being particularly effective.
• the polyoxyalklene compounds used may be any compounds which may be derived from ethylene oxide, propylene oxide or mixtures thereof and which are capable of imparting permanent antistatic properties to polyamides when used on their own in quantities of up to 7 %, by weight.
• Polyethers of the polyethylene oxide series are preferred because of their particularly powerful effect.
• polyethers which contain functional groups are also suitable for use in the polyamide compositions of the present invention. Examples of these are alkoxylated alcohols, carboxylic acids, amines, phenols or substituted phenols.
• polyethers or polyether derivatives which have a good antistatic effect on polyamides when used alone are particularly suitable for use, in combination with the carboxylic acid amides, according to the invention.
• the relative viscosities indicated refer to a 1 % solution of the polyamide in m-cresol at 25°C.
• the electrical surface resistance was measured with a high resistance ohmmeter on fibers after removal of the spinning preparation by washing at 60°C in a solution of 5 g per liter of an alkaline detergent, drying and 48 hours conditioning in a standard atmosphere of 50 % relative humidity at 23°C. The washings and measurements were carried out 10 times.
• the degree of whiteness of the fibers was measured after various periods at 140°C.
• a polycaprolactam melt, ( ⁇ rel . 2.60), in which 1 %, by weight, of a 20-fold ethoxylated oleyl alcohol is already homogeneously distributed is mixed with 1 %, by weight, based on the polycaprolactam, of N,N'-dilauroyl-N-isopropyl-diamino-hexane by adding the latter from a feed screw to the polycaprolactam which is in a double shaft extruder. The mixture is spun to form filaments of dtex 100 f 25.
• the electrical surface resistance of the stretched material is 9 ⁇ 10 9 ohm after the first washing and 2 ⁇ 10 10 ohm after the 10th washing.
• Filaments with a titer of dtex 100 f 25, manufactured as in Example 1, containing only 2 %, by weight, of the 20-fold ethoxylated oleyl alcohol is found to have a surface resistance of 8 ⁇ 10 10 ohm after the first washing and 2 ⁇ 10 11 ohm after the 10th washing.
• the filaments obtained have a surface resistance of 8 ⁇ 10 11 ohm after the first washing and 2 ⁇ 10 12 ohm after the 10th washing.

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• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• Compositions Of Macromolecular Compounds (AREA)
• Artificial Filaments (AREA)
• Extrusion Moulding Of Plastics Or The Like (AREA)
• Manufacture Of Macromolecular Shaped Articles (AREA)

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Cited By (4)

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Citations (6)

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• 1973
  • 1973-05-16 DE DE2324689A patent/DE2324689A1/de active Pending
• 1974
  • 1974-05-14 GB GB2119874A patent/GB1435637A/en not_active Expired
  • 1974-05-14 IT IT22698/74A patent/IT1017608B/it active
  • 1974-05-14 ES ES426300A patent/ES426300A1/es not_active Expired
  • 1974-05-14 DD DD178493A patent/DD115146A5/xx unknown
  • 1974-05-14 LU LU70076A patent/LU70076A1/xx unknown
  • 1974-05-15 JP JP49053447A patent/JPS5019854A/ja active Pending
  • 1974-05-15 DK DK266874A patent/DK136428C/da active
  • 1974-05-15 IE IE1037/74A patent/IE39268B1/xx unknown
  • 1974-05-15 BE BE144331A patent/BE815053A/xx unknown
  • 1974-05-16 NL NL7406597A patent/NL7406597A/xx unknown
  • 1974-05-16 US US05/470,495 patent/US3962176A/en not_active Expired - Lifetime
  • 1974-05-16 FR FR7417087A patent/FR2229732B1/fr not_active Expired

Patent Citations (6)

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